DE3856431T2 - Acrylsäure-Derivate als Fungizide - Google Patents
Acrylsäure-Derivate als FungizideInfo
- Publication number
- DE3856431T2 DE3856431T2 DE3856431T DE3856431T DE3856431T2 DE 3856431 T2 DE3856431 T2 DE 3856431T2 DE 3856431 T DE3856431 T DE 3856431T DE 3856431 T DE3856431 T DE 3856431T DE 3856431 T2 DE3856431 T2 DE 3856431T2
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- ring
- optionally substituted
- substituted
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
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- 239000000417 fungicide Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- -1 tetrazofyl Chemical group 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 19
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- 238000002360 preparation method Methods 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
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- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
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- 125000002541 furyl group Chemical group 0.000 claims description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NCEIEWKQCZHKNX-RVDMUPIBSA-N methyl (e)-2-[2-(1,3-benzothiazol-2-ylsulfanylmethyl)phenyl]-3-methoxyprop-2-enoate Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1CSC1=NC2=CC=CC=C2S1 NCEIEWKQCZHKNX-RVDMUPIBSA-N 0.000 description 1
- ZXUQEPZWVQIOJE-UHFFFAOYSA-N methyl 2-chloro-2-oxoacetate Chemical compound COC(=O)C(Cl)=O ZXUQEPZWVQIOJE-UHFFFAOYSA-N 0.000 description 1
- GYVCWIWGYQGQCP-UHFFFAOYSA-N methyl 2-imidazol-1-yl-2-oxoacetate Chemical compound COC(=O)C(=O)N1C=CN=C1 GYVCWIWGYQGQCP-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
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- C07—ORGANIC CHEMISTRY
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- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- Chemical & Material Sciences (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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GB878716392A GB8716392D0 (en) | 1987-07-11 | 1987-07-11 | Fungicides |
GB888807388A GB8807388D0 (en) | 1988-03-29 | 1988-03-29 | Fungicides |
Publications (2)
Publication Number | Publication Date |
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DE3856431D1 DE3856431D1 (de) | 2000-11-16 |
DE3856431T2 true DE3856431T2 (de) | 2001-02-08 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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DE3856431T Expired - Fee Related DE3856431T2 (de) | 1987-07-11 | 1988-07-11 | Acrylsäure-Derivate als Fungizide |
Country Status (18)
Country | Link |
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US (2) | US5192357A (sh) |
EP (1) | EP0299694B1 (sh) |
JP (1) | JP2688495B2 (sh) |
KR (1) | KR960012207B1 (sh) |
CN (1) | CN1025649C (sh) |
AT (1) | ATE196900T1 (sh) |
AU (1) | AU607235B2 (sh) |
BR (1) | BR8803436A (sh) |
DE (1) | DE3856431T2 (sh) |
DK (1) | DK381588A (sh) |
FI (1) | FI92392C (sh) |
HU (1) | HU204658B (sh) |
IL (1) | IL87020A (sh) |
NZ (1) | NZ225339A (sh) |
PT (1) | PT87938B (sh) |
TR (1) | TR24201A (sh) |
YU (1) | YU47288B (sh) |
ZW (1) | ZW9388A1 (sh) |
Families Citing this family (60)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0391451A1 (en) * | 1986-04-17 | 1990-10-10 | Imperial Chemical Industries Plc | Fungicides |
GB8724252D0 (en) * | 1987-10-15 | 1987-11-18 | Ici Plc | Fungicides |
US5194438A (en) * | 1988-07-15 | 1993-03-16 | Basf Aktiengesellschaft | α-arylacrylates substituted by a trifluoromethylpyrimidinyloxy radical, fungicidal compositions and methods |
DE3823991A1 (de) * | 1988-07-15 | 1990-02-15 | Basf Ag | Heterocyclisch substituierte (alpha)-aryl-acrylsaeureester und fungizide, die diese verbindungen enthalten |
DE3835028A1 (de) * | 1988-10-14 | 1990-04-19 | Basf Ag | Oximether-derivate, verfahren zu ihrer herstellung und diese enthaltende fungizide |
DE3836581A1 (de) * | 1988-10-27 | 1990-05-03 | Basf Ag | Heterocyclisch substituierte (alpha)-aryl-acrylsaeuremethylester und ihre verwendung |
DE3838094A1 (de) * | 1988-11-10 | 1990-05-17 | Nordmark Arzneimittel Gmbh | Feste pharmazeutische retardform |
GB8828543D0 (en) * | 1988-12-07 | 1989-01-11 | Ici Plc | Insecticides |
DE3843439A1 (de) * | 1988-12-23 | 1990-06-28 | Basf Ag | Schwefelhaltige oximether und diese enthaltende fungizide |
DE69026395T2 (de) * | 1989-01-11 | 1997-03-06 | Agrevo Uk Ltd | Acrylat-Fungizide |
DE3901607A1 (de) * | 1989-01-20 | 1990-08-16 | Basf Ag | Schwefelhaltige acrylsaeureester und diese enthaltende fungizide |
DE3904931A1 (de) * | 1989-02-17 | 1990-08-23 | Bayer Ag | Pyridyl-substituierte acrylsaeureester |
CA2015981A1 (en) * | 1989-05-10 | 1990-11-10 | Thomas H. Brown | Compounds |
FR2647787B1 (fr) * | 1989-06-06 | 1991-09-27 | Roussel Uclaf | Nouveaux thiazolylalkoxyacrylates, leur procede de preparation, leur application comme fongicides et leurs intermediaires de preparation |
DE3923068A1 (de) * | 1989-07-13 | 1991-01-24 | Basf Ag | Verfahren zur bekaempfung von schaedlingen mittels substituierter pyrimidine |
DE4014420A1 (de) * | 1989-09-23 | 1991-04-04 | Bayer Ag | 5h-furan-2-on-derivate |
US5207817A (en) * | 1989-09-23 | 1993-05-04 | Bayer Aktiengesellschaft | Herbicidal 5H-furan-2-one derivatives |
US5112860A (en) * | 1989-11-16 | 1992-05-12 | Basf Aktiengesellschaft | Thiocarboxylic esters and fungicides containing them |
US5187170A (en) * | 1989-11-16 | 1993-02-16 | Basf Aktiengesellschaft | Thiocarboxylic esters and fungicides containing them |
GB9009916D0 (en) * | 1990-05-02 | 1990-06-27 | Schering Agrochemicals Ltd | Preparation of acrylic acid derivatives |
ZA913760B (en) * | 1990-05-24 | 1992-02-26 | Sumitomo Chemical Co | Pyridine derivatives,their production processes and their compounds for control of insect pests |
DE69104961T2 (de) * | 1990-12-06 | 1995-03-16 | Roussel Uclaf | Anwendung von Thiazolylalkoxyacrylaten in der Herstellung von Insektiziden und/oder Akanizide-Zusammensetzungen. |
FR2674246B1 (fr) * | 1991-03-21 | 1993-07-09 | Roussel Uclaf | Nouveaux derives de l'acide alpha-methylene 5-thiazolacetique, leur procede de preparation et les intermediaires de ce procede, leur application a titre de fongicides et les compositions les renfermant. |
BR9206069A (pt) * | 1991-06-05 | 1994-12-27 | Schering Agrochemicals Ltd | Composição fungicida e processo de combater fungos fitopatogênicos |
DE4216814A1 (de) * | 1991-07-16 | 1993-01-21 | Bayer Ag | 3-aryl-4-hydroxy-(delta)(pfeil hoch)3(pfeil hoch)-dihydrofuranon- und 3-aryl-4-hydroxy-(delta)(pfeil hoch)3(pfeil hoch)-dihydrothiophenon-derivate |
GB9218541D0 (en) * | 1991-09-30 | 1992-10-14 | Ici Plc | Fungicides |
GB9122098D0 (en) * | 1991-10-17 | 1991-11-27 | Ici Plc | Fungicides |
KR970006247B1 (en) * | 1992-09-28 | 1997-04-25 | Lg Chemical Ltd | Novel benzothiazole derivatives and process for preparing the same |
GB9320744D0 (en) * | 1992-11-04 | 1993-12-01 | Zeneca Ltd | Oxa and thiadiazole derivatives |
ES2068737A1 (es) * | 1992-12-14 | 1995-04-16 | Schering Agrochemicals Ltd | Derivados del acido propenoico. |
DE4305502A1 (de) * | 1993-02-23 | 1994-08-25 | Basf Ag | Ortho-substituierte 2-Methoxyiminophenylessigsäuremethylamide |
ES2108897T3 (es) * | 1993-03-19 | 1998-01-01 | Ube Industries | Compuesto del tipo oxima eter, procesos para su preparacion y fungicida que contiene dicho compuesto. |
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IL115899A (en) * | 1994-11-17 | 2002-07-25 | Basf Aktiengesellshaft | History of Acid-2 [(2-alkoxy-6-trifluoromethyl-pyrimidine-4-yl) oxymethylene] -phenylate, their preparation, preparations for the control of animal and fungal pests containing these histories and a number of their intermediates |
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DE19519041A1 (de) * | 1995-05-24 | 1996-11-28 | Basf Ag | Azolyloxybenzyl-alkoxyacrylsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung |
IL122715A (en) * | 1995-06-28 | 2000-11-21 | Zeneca Ltd | Process for the preparation of 2-(6-substituted-pyrid-2-yloxymethyl)phenylacetates useful as intermediates for producing fungicides |
GB9519787D0 (en) * | 1995-09-28 | 1995-11-29 | Sandoz Ltd | Organic compounds |
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US6084120A (en) * | 1997-07-09 | 2000-07-04 | Hoffmann-La Roche Inc. | β-Alkoxyacrylates against malaria |
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AU2298999A (en) * | 1998-02-05 | 1999-08-23 | Nippon Soda Co., Ltd. | Thiazole compounds, production process, pest control agent, and antifungal agent |
FR2777002A1 (fr) * | 1998-04-07 | 1999-10-08 | Rhone Poulenc Agrochimie | Nouveaux composes fongicides |
FR2777003A1 (fr) * | 1998-04-07 | 1999-10-01 | Rhone Poulenc Agrochimie | Nouveaux composes fongicides |
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CN101205187B (zh) * | 2006-12-22 | 2011-04-27 | 中国中化股份有限公司 | 取代芳基醚类化合物及其制备与应用 |
CN101311170B (zh) | 2007-05-25 | 2010-09-15 | 中国中化股份有限公司 | 取代嘧啶醚类化合物及其应用 |
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CN101906075B (zh) | 2009-06-05 | 2012-11-07 | 中国中化股份有限公司 | 含取代苯胺基嘧啶基团的e-型苯基丙烯酸酯类化合物及其应用 |
CN108314656B (zh) | 2018-02-27 | 2020-10-27 | 浙江工业大学 | 不饱和烃嘧啶硫醚类化合物及其制备方法与应用 |
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NZ213630A (en) * | 1984-10-19 | 1990-02-26 | Ici Plc | Acrylic acid derivatives and fungicidal compositions |
DE3519282A1 (de) * | 1985-05-30 | 1986-12-04 | Basf Ag, 6700 Ludwigshafen | Acrylsaeureester und fungizide, die diese verbindungen enthalten |
DE3519280A1 (de) * | 1985-05-30 | 1986-12-04 | Basf Ag, 6700 Ludwigshafen | Stilbenderivate und fungizide, die diese verbindungen enthalten |
DE3545319A1 (de) * | 1985-12-20 | 1987-06-25 | Basf Ag | Acrylsaeureester und fungizide, die diese verbindungen enthalten |
DE3545318A1 (de) * | 1985-12-20 | 1987-06-25 | Basf Ag | Acrylsaeurederivate und fungizide, die diese verbindungen enthalten |
EP0391451A1 (en) * | 1986-04-17 | 1990-10-10 | Imperial Chemical Industries Plc | Fungicides |
DE3620860A1 (de) * | 1986-06-21 | 1987-12-23 | Basf Ag | Substituierte acrylsaeureester und fungizide, die diese verbindungen enthalten |
GB8617648D0 (en) * | 1986-07-18 | 1986-08-28 | Ici Plc | Fungicides |
EP0260832A3 (en) * | 1986-09-16 | 1990-06-13 | Imperial Chemical Industries Plc | Insecticides |
ES2052696T5 (es) * | 1987-02-09 | 2000-03-01 | Zeneca Ltd | Fungicidas. |
-
1988
- 1988-07-06 IL IL8702088A patent/IL87020A/en not_active IP Right Cessation
- 1988-07-06 YU YU131888A patent/YU47288B/sh unknown
- 1988-07-07 AU AU18806/88A patent/AU607235B2/en not_active Ceased
- 1988-07-08 TR TR88/0509A patent/TR24201A/xx unknown
- 1988-07-08 NZ NZ225339A patent/NZ225339A/xx unknown
- 1988-07-08 PT PT87938A patent/PT87938B/pt not_active IP Right Cessation
- 1988-07-08 DK DK381588A patent/DK381588A/da not_active Application Discontinuation
- 1988-07-08 US US07/216,831 patent/US5192357A/en not_active Expired - Fee Related
- 1988-07-08 HU HU883617A patent/HU204658B/hu not_active IP Right Cessation
- 1988-07-08 BR BR8803436A patent/BR8803436A/pt not_active IP Right Cessation
- 1988-07-08 ZW ZW93/88A patent/ZW9388A1/xx unknown
- 1988-07-11 DE DE3856431T patent/DE3856431T2/de not_active Expired - Fee Related
- 1988-07-11 KR KR1019880008571A patent/KR960012207B1/ko not_active IP Right Cessation
- 1988-07-11 CN CN88104241A patent/CN1025649C/zh not_active Expired - Fee Related
- 1988-07-11 EP EP88306296A patent/EP0299694B1/en not_active Expired - Lifetime
- 1988-07-11 JP JP63171074A patent/JP2688495B2/ja not_active Expired - Lifetime
- 1988-07-11 AT AT88306296T patent/ATE196900T1/de not_active IP Right Cessation
- 1988-07-11 FI FI883297A patent/FI92392C/fi not_active IP Right Cessation
-
1993
- 1993-01-19 US US08/005,284 patent/US5304530A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
FI883297A (fi) | 1989-01-12 |
EP0299694A2 (en) | 1989-01-18 |
HU204658B (en) | 1992-02-28 |
TR24201A (tr) | 1991-07-01 |
ZW9388A1 (en) | 1989-02-01 |
IL87020A (en) | 1996-09-12 |
PT87938A (pt) | 1989-06-30 |
DK381588D0 (da) | 1988-07-08 |
DE3856431D1 (de) | 2000-11-16 |
DK381588A (da) | 1989-01-12 |
NZ225339A (en) | 1990-05-28 |
YU131888A (en) | 1990-12-31 |
HUT47373A (en) | 1989-03-28 |
JPS6431746A (en) | 1989-02-02 |
FI92392C (fi) | 1994-11-10 |
YU47288B (sh) | 1995-01-31 |
JP2688495B2 (ja) | 1997-12-10 |
EP0299694B1 (en) | 2000-10-11 |
KR960012207B1 (ko) | 1996-09-16 |
FI883297A0 (fi) | 1988-07-11 |
US5304530A (en) | 1994-04-19 |
CN1025649C (zh) | 1994-08-17 |
ATE196900T1 (de) | 2000-10-15 |
FI92392B (fi) | 1994-07-29 |
PT87938B (pt) | 1995-03-01 |
IL87020A0 (en) | 1988-12-30 |
AU1880688A (en) | 1989-01-12 |
BR8803436A (pt) | 1989-01-24 |
KR890002091A (ko) | 1989-04-08 |
US5192357A (en) | 1993-03-09 |
AU607235B2 (en) | 1991-02-28 |
CN1031227A (zh) | 1989-02-22 |
EP0299694A3 (en) | 1989-11-29 |
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